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WILLIAMSTOWN — “This being a tourist is exhausting,’’ said Bettye Wehrli. And I had to agree.

It’s day four of a jam-packed tour, The Best of Massachusetts Art: Boston and the Berkshires. I’m tagging along with the Naperville Community Associates of the Art Institute of Chicago, a group with endless enthusiasm and stamina whose itinerary includes visiting nine museums, two historic homes, and one gallery in five days, squeezing in as much art appreciation as possible. It’s a fine arts marathon, so to speak, which leaves me wishing I had squeezed a pair of sneakers into my suitcase.

“We’re the Midwest museum warriors!’’ said Joan Myers, who — I can’t help but notice — is wearing sensible shoes.

My contribution to this tour, conceived and choreographed by Meg MacDonald of Travel Muse, is to assist counting heads (42) each time the bus departs a destination, and ensure everyone is properly hydrated by handing out bottles of water.

In between, I’ve seen a plethora of terrific art in a dizzying array of styles from 16th-century tapestries, to Edo Period Japanese prints, to sculpture made of light, to meticulously painted scenes of tall ships sailing in tranquil harbors. We’ve perused works by Monet, Degas, LeWitt, Horn, Sargent, Avery, Prendergast, Avedon, Rembrandt, and Matta — a partial list — and are cruising to the finish line with only the Norman Rockwell Museum left on the schedule.

This might sound crazy, but the trip has been quite fun.

At each destination, we break into smaller groups and follow docents or guides through the museums. Although our tours were prearranged, most venues offer scheduled gallery talks as part of their ticket price, so this itinerary can be reproduced, with or without 40 of your closest friends.

DAY 1:

We begin at the Isabella Stewart Gardner Museum in Boston, an eclectic collection housed in a Venetian-style palace. Our docent explains that looking closely at art improves critical skills. So rather than speeding through the galleries, we spend time discussing several key works, with our docent asking questions such as, “What do you notice about the person in this portrait?’’ and “Why do you think this painting created a scandal?’’ I’m busy scribbling notes when a museum guard taps me on the shoulder and offers a pencil. No pens allowed.

In the late afternoon, we saunter over to the family-run Vose Galleries of Boston on Newbury Street, a multilevel gallery featuring American paintings from the 18th through 20th centuries, and a good introduction to the works we’ll see in Salem and Gloucester.

DAY 2

The Peabody Essex Museum in Salem opens at 10 a.m. and we arrive then for the “Highlights of the Collection Tour,’’ a one-hour zip through this museum that showcases decorative arts, paintings, costumes, and textiles from North America, China, Japan, Korea, India, and beyond, as well as an extensive collection of maritime art and culture.

Our docent does an admirable job, discussing several works in depth, especially the Chinese moon bed, an elaborately carved round structure inlaid with ivory. One renegade group member abandons the tour, paying extra for a headset and ticket to the Yin Yu Tang house, a 200-year-old merchant’s home transported from China and reassembled in the museum.

At the end of the tour, most of the group makes a beeline to the gift shop. As we board the coach, ready for lunch in Rockport, I notice arms laden with shopping bags.

“Maybe I should design a Gift Shops of the World Tour. Museums optional,’’ quipped MacDonald.

At the Cape Ann Museum in Gloucester, described by our docent as “a big little museum,’’ the history, art, and culture of the region are told through artifacts, historical photographs, and fine and decorative arts collections from the 18th century through the 20th. We view intricate paintings of maritime luminist artists such as Fitz Henry Lane, and also see the tools, equipment, and models of the fishing industry and maritime trade.

Then before one can say, “Is the gift shop open?’’ it’s time to head south to the Institute of Contemporary Art, the other end of the artistic spectrum.

Located on Fan Pier, the ICA exhibits contemporary art in all media. Though, on the whole, this group’s taste in art runs more to traditional than cutting-edge, no one raises an eyebrow as our transgender guide — in fishnets and heels — deftly guides us through the “Roni Horn a.k.a. Roni Horn’’ exhibition, as well as galleries featuring work by Mexican tattoo artist Dr. Lakra. The one-hour tour leaves a little time for viewing the permanent collection. Sadly, the gift shop is closed as we finish at 5 p.m.

DAY 3

After a quick trip to Cambridge to check out the Frank Gehry building at the Massachusetts Institute of Technology, spirits are high as we cruise to the Museum of Fine Arts in Boston for the “Masterpieces’’ tour. This quick overview of the museum’s greatest hits whets my appetite to return, and has me wondering how the out-of-towners are coping.

“I have some background in art,’’ said Joanne Nadelhoffer. “It’s hard to not stop and look at everything that interests you. There’s a tension between wanting to go back and look, and listening to the speaker. I love it.’’

“You always wish you could see a little more,’’ said Nancy Hill.

With that in mind, some eschew lunch, grabbing a snack-to-go in the cafeteria for a picnic later on the bus, while others dine leisurely in the first-floor cafe, and make good use of time in the museum store. Then it’s off to Western Massachusetts.

In Stockbridge, we tour the grounds and house of Naumkeag, the 44-room summer retreat of Joseph Hodges Choate designed by the architectural firm McKim, Mead and White in 1885. Then it’s on to Chesterwood to visit the country home and studio of Daniel Chester French, a preeminent sculptor of public monuments best known for his towering marble sculpture of Abraham Lincoln at the Lincoln Memorial in Washington.

DAY 4:

The Stone Hill Center, designed by Japanese architect Tadao Ando, isn’t open but we peek in the windows, and view the Juan Muñoz sculptures on the terrace before walking down a woodland path to the Sterling and Francine Clark Art Institute in Williamstown. Here, our guides lead us through the collection that includes paintings, porcelain, silver, prints, and drawings from the 14th century to the 19th, featuring the works of French Impressionists like Renoir, and the Barbizon School. My feet are screaming in the heels that, this morning, were the only comfortable shoes left to wear of the three pairs I packed.

At the Massachusetts Museum of Contemporary Art, in North Adams, I’m asked, “Does an artist need to be crazy to make art?’’

“No. That’s a myth,’’ I said. But I begin to wonder, as we wander through cavernous exhibitions of contemporary art, whether one needs to be crazy to embark on a trip like this. After three floors of Sol LeWitt wall paintings, and seven site-specific installations aptly titled “Material World,’’ I’m in a kind of art-induced coma.

A shot of espresso and a brownie at the cafe pick me up as we head to the Williams College Museum of Art. And who can be lethargic when John Stomberg, the deputy director of the museum, steps in to lead our tour?

“There’s a thesis to each gallery,’’ said Stromberg. His lecture on Matta’s paintings, which mine interior consciousness in a manner “akin to psychoanalysis in history,’’ makes me want to enroll in school again. As we head upstairs, I slip out of my heels and pad around in my socks, hoping no one will notice.

DAY 5:

The Norman Rockwell Museum is the last stop. It houses a large collection of the artist’s work and we can view his studio.

After a grand farewell lunch, we clamber onto the bus for the Albany, N.Y., airport, where the group will fly back to Chicago.

“It’s been an action-packed five days. It’s a great overview,’’ said Judy Kovarik.

“We’ve seen a wide range of art,’’ said Myers. “The mood of the people was affected by each previous two-hour experience. We came out of the Rockwell Museum all warm and fuzzy. At Mass MoCA we were totally energized. The Clark, serene. People absolutely loved it. Certainly art changes your mindset and mood.’’

Do you have to be crazy to plan such a trip? Not at all. Just pack the right shoes.